Park Slut (ch. 3)
By Alleykat 30 Nov 2021
Turned into the park cocksucker by a fat old man
Gay Crossdresser Stories
GayDemon's Stories: On this page you can find erotic fiction where you can read about men dressing up as women and gay sex with transvestites and crossdressers.
Jessi’s debut - A true Jessi story
By JohnRain24601 25 Nov 2021
John goes out as Jessi for the first time - to a party at an adult book store.
Chis(topher) & Chris(tina) (ch. 2)
By djfmonkey 23 Nov 2021
Chapter 2. - Chris and I meet the grandparents
Park Slut (ch. 3)
By Alleykat 23 Nov 2021
I would go to the park at night letting guys blow me until the fat old man turned me into the cocksucking cumloving slut at the park and at my mom's house.
Chis(topher) & Chris(tina)
By djfmonkey 22 Nov 2021
I met and fell for a crossdresser, explore chapter 1 introducing us, and future chapters meeting family and friends
Now I'm a crossdressing Domme?
By BillyBoy 20 Nov 2021
A shy, submissive guy hits me up to dress like his wife and Domme him. I actually liked it more than I thought I would!
How this straight guy became a sissy bottom
By Somewhat Straight 17 Nov 2021
It took while, but my transformation is complete
Doctors are human too
By BillyBoy 11 Nov 2021
I forgot and wore some panties to my check-up. The doc was surprised. But he responded differently than I expected.
blow and go buddy gets kinky
By BillyBoy 10 Nov 2021
Joe was always pretty much a Dom. But he seemed to figure out I'd do pretty much anything to suck him off. So he just keeps pushing. Now I have to go out and buy some items he requested. And that is a whole other story!
In a short span I became a sissy boy trap (ch. 2)
By Desertbiguy 10 Nov 2021
I had spent all of my time getting indoctrinated in gay sex by Tom G. I forgot about my first man to pop my anal cherry Mark.
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Introduction into Gay Domination (ch. 2)
By Anthony 8 Nov 2021
I went to work and tried not to run into Jerry, but that was hard, seemed like Jerry kept looking over at me and would walk by me giving me a look. When no one was around, he would come up to me and show me a picture of me on his phone of me in one of the positions that I was in.
Tranny at the bar
By djfmonkey 8 Nov 2021
The best looking girl in the bar was a guy and I love her.
Nanny cam gone bad
By BillyBoy 5 Nov 2021
My wife installed one of those nanny cams. She wanted to see what the dog was doing when we were at work. She didn't tell me. She started watching me dress in her underclothes and tie myself up like a kidnap victim, jerking off. Not sure what to do, she asked a friend to watch the videos. He knew just what to do with me.
Crossdressing
By BillyBoy 2 Nov 2021
Envious of the girls always getting to wear those cute little bras and panties.
Halloween is a great time to express sexual feelings
By Desertbiguy 2 Nov 2021
I decided to dress up as a girl for halloween. There was a big party going on for us jr high kids. And looked good. Maybe to good. Mark was a good looking guy. Something happened at party. He became attracted to me.
Becoming the Fishing Camp Princess
By Dickguy4U2 31 Oct 2021
While well over the legal age of sexual consent, my looks represented a much different picture. Broght up by a single parent overbearing mother, my being raised was far from the normal channels of a lone single male son.With mom making dresses and me the perfect slender size to model her creations, I guess you could say that the soft silk and lace never failed to stimulate me in a secret sexy way
A Halloween story
By BillyBoy 28 Oct 2021
Dressed up for Halloween and nowhere to go. Until I get invited to a last-minute party.
Macy's gay parade
By BillyBoy 23 Oct 2021
The clerk at Macy's gave me a strange look as he checked out the lingerie I was buying.
Prom night for a sissy crossdresser
By BillyBoy 19 Oct 2021
I meet a cute sissy out for prom night. But he needs a date.
Getting fucked by grinder date in hotel
By zeenatcd 18 Oct 2021
I met one mature men on grindr and and then we enjoyed a lot in hotel room. He fucked my 2 times in row continuously. Then he became my fantasy partner.
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The crossdresser
By BillyBoy 16 Oct 2021
Silly me gets seduced by a pretty closet crossdresser. I help her come out, so to speak. And I have a nice time as well.
working my way up to a complete sissy tramp
By BillyBoy 13 Oct 2021
A pervert friend takes me from my first hand-job, up through the progression to where I was escorting him out to bars as a woman.
scary trying to be yourself
By BillyBoy 12 Oct 2021
I thought wearing my sister's underwear made me gay. I was worried about that. But it didn't. But finding someone who wasn't repulsed seeing me in her stuff was very difficult. Until now.
I'm a gay sissy transgender fuck toy
By BillyBoy 9 Oct 2021
When I came back from California, changed into a Caitlyn, I was surprised how many of my old schoolmates and teachers were trying to get in touch.
I married a fat girl
By BillyBoy 8 Oct 2021
I only found out much later that she set me up to catch me in her undies and tricked me into becoming a sissy peg boy and later a slut for her x boyfriend who she was still fucking. I guess that is the whole story, actually!
first time caught in hers
By BillyBoy 6 Oct 2021
Wife catches me the first time. Very embarassing. But not at all as bad as when she turns me over to the kinky gay guy she works with.
diapered like a helpless bitch
By BillyBoy 5 Oct 2021
Joe found my personal chats and used them to blackmail and abuse me. I loved it!
An interactive fantasy game
By BillyBoy 1 Oct 2021
Going to a hotel dating game is different when all the people are matched up to their kinky fetishes and fantasies.
What is a cockold? Now I think I know.
By BillyBoy 30 Sep 2021
My first wife was a bitch. She put me through hell. But the second one put me through something worse. Watching her boyfriend fuck her while I was bound and gagged and tied to a chiar in the bedroom. Maybe my third wife will be nice to me.
i guess you could say she seduced me
By BillyBoy 29 Sep 2021
I met her at the hotel bar. There was a crossdressing convention there that weekend. I didn't know it. But I found out soon enough.
caught crossdressing
By BillyBoy 28 Sep 2021
im not very fem but i love to wear panties. A golfing partner saw my profile on a webite like this and made the most of my situation.
Bathhouse Frenzy (ch. 2)
By popperboi 25 Sep 2021
A young virgin continues his first bathhouse experience. Fortunately a Masterful Black Daddy takes him under his wing
A Trip to the Grocery store (ch. 2)
By Don 18 Sep 2021
How my life change forever
A Trip to the Grocery store
By Don 17 Sep 2021
How a trip to grocery store changed my life.
Another Bookstore Experience
By MontanaBiGuy 17 Sep 2021
Alone in a bookstore and got surprised with my cock in my hand